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The 10 Most Infamous Bars in America

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Belly up like a badass at one of these watering holes made famous by ghosts, gangs, pirates or prostitution rings. A new travel book shows you exactly where to stop.

by
Hollis Templeton 1 / 11

When a full day of travel leaves you thirsty for a stiff drink, you could hit up a hotel bar and enjoy a watered-down Old Fashioned or one of three beers on tap. Or you could unwind at a watering hole where Al Capone, Jack Kerouac or Clark Gable once sat.

We don’t know about you, but we’d go with the latter. That’s why we’re psyched about a new travel book called Bucket List Bars, in which friends and history buffs Dr. Clint Lanier and Derek Hembree, explore the backstories of 40 of the most famous (and infamous) bars in America.

We recently sat down with the authors and got right to the good stuff—watering holes best known for hauntings, prostitution rings, smugglers' dens, and mafia activity. If you’re ready to belly up like a badass, make sure one of these 10 bars makes its way onto your summer bucket list.

New York, New York

Heaps of nautical artifacts speak to the history of the waterfront bar—Ear Inn was an ideal spot for sailors, immigrant gangs, and river pirates to throw back glasses of corn whisky in the 1800s and early 1900s. During Prohibition, a brothel occupied the speakeasy’s second and third floors, and today the bar is rumored to be haunted, with the top floor reportedly being the ghost’s favorite hangout.

And, believe it or not, the watering hole’s notorious past has nothing to do with ears. To avoid a lengthly review by the Landmark Commission—the group was picky about new signs being added to historic buildings—the owners simply painted over part of the B in “Bar” to give the nameless establishment an official title.

New York, New York

Another pre-Prohibition hotspot for criminals, pirates, and men seeking the short-term company of a woman, Bridge Café is New York City’s oldest alcohol-serving establishment. It’s also rumored to be one of the most haunted watering holes in the city. Loud footsteps can reportedly be heard coming from the empty second floor, stereos turn themselves up and down, and computers are constantly crashing. Still, despite the spookiness, the former brothel and grog shop has been transformed into an upscale café, complete with white tablecloths, gourmet food, and an extensive offering of single malts, bourbons, and rye whiskies.

Chicago, Illinois

Known for serving whisky-spiked coffee during the Prohibition Era, the decades-old speakeasy is rumored to be home to a revenge-seeking spirit. Where’d she come from? Simon Lumberg, a Swedish immigrant who opened up the bar in Chicago’s Andersonville neighborhood during the 1920s, had a son named Roy Lumberg, who stirred up some family drama when he had intimate relations with a married woman. That woman died in a car accident while traveling with Roy, and years later, right after Roy’s death, his image was found mysteriously cut out of a family mural that spans one side of the bar. Today, some patrons say they can sense the spirit’s presence while sitting at the bar.

Tombstone, Arizona

Situated on one of the Wild West’s bloodiest street corners, Crystal Palace is riddled with bullet holes, evidence of the countless shootouts that took place at the saloon throughout history. Today, tourists flock to the dusty mining-town watering hole to see period gunfight reenactments and servers dressed in authentic Old-West attire. Ghost hunters also frequent the bar, as patrons report paranormal activity, like lights randomly turning off and on and relic gambling wheels spinning without being touched.

Hollywood, California

The Frolic Room’s darkest secret is rooted in one of the city’s most famous murder mysteries—the Black Dalia. On January 15, 1947, the body of the Black Dalia, whose real name was Elizabeth Short, was found gruesomely mangled and cut in half at a nearby park. Next to nothing is known about the Black Dalia’s killer or his intentions. One detail about the unsolved murder that has been solidified: the Frolic Room was Short’s favorite bar and one of the last places she was seen alive.

Austin, Texas

During the Prohibition Era, The Tavern served as a grocery store by day and a speakeasy, gambling hall, and brothel by night. Although the brothel’s been shut down for years, the spirit of a hostess named Emily is rumored to live on inside the oldest sports bar in Texas. Emily was killed during a fight that broke out between two patrons in the 1940s. Today, visitors report seeing apparitions of Emily staring out of a second floor window late at night. To solidify their stories, a pair of shoes that were discovered during a renovation—and rumored to have belonged to Emily—are displayed on the second floor.

San Antonio, Texas

Situated on San Antonio’s famous River Walk, the post-Prohibition saloon was popular among members of the Mexican Mafia, a group of street thugs who ran drug and prostitution rings out of the tavern—and even designated a loft in the back of the bar as a champagne room—between the 1970s and 2006, when The Esquire closed its doors. After a taking five years to clean up its image as a rough place with a rough crowd—the bar had metal detectors and sold shirts that said “I Survived The Esquire Tavern”—the watering hold reopened in 2011 with a new identity. Today, patrons at the now fully renovated venue enjoy vintage-inspired décor and traditional cocktails—sans stabbings, shootings, and bar fights.

Goodsprings, Nevada

The Pioneer Saloon is located 30 miles from the Las Vegas Strip, but a trip to the old-school saloon is definitely worth the drive. Tin walls are punctured with bullet holes reminiscent of a particularly rowdy night. What went down: a gambler was caught cheating and made a move to kill the dealer. The dealer drew a pistol in self-defense and shot the cheater twice in the head. The bullets passed through the gambler—and through the wall behind him, where they remain today.

The saloon is also where actor Clark Gable spent three straight days drinking and smoking cigars while he waited for his wife’s remains to be retrieved from the nearby mountains following a deadly plane crash (you can still see burn marks from his cigar on the bar).

Denver, Colorado

Rowdy patrons usually give a bar its bad rap, but El Chapultepec’s owner got a reputation for being just as hard-nosed and mean as his clientele—if not more so. To compensate for his 5’4” stature, the now deceased Jerry Krantz stashed a baseball bat behind the bar and used it to keep unruly patrons in line. When a judge threatened jail time, Krantz switched his weapon of choice to a sock with a cue ball in it. Today, “The Pec” is a safer place. The dive bar is a good spot to see live jazz (Krantz was a huge fan), settle into the famous booth where Jack Keroac once mused or grab a cold beer after a Colorado Rockies game—Coors Field is across the street.

Chicago, Illinois

Walking into Green Mill is like transporting yourself back to a 1920s speakeasy. Decked out in period furniture and décor from the Roaring Twenties, the jazz club was Al Capone’s favorite hangout (you can still sit in his booth today). Not surprisingly, the speakeasy’s got some noteworthy gang activity on the books: Jack McGurn, one of the owners, was known for using intimidation, bribery, blackmail, and violence to gain a stake in clubs across Chicago. When Joe E. Lewis, one of Green Mill’s most profitable acts, moved on and opened another venue, McGurn hired a hit man to beat him up—and cut out part of his tongue. Despite his injuries, Lewis survived the attack, and his recovery is rumored to have been funded by Capone.